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Details

Stereochemistry ACHIRAL
Molecular Formula C15H18
Molecular Weight 198.3034
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GUAIAZULENE

SMILES

CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1

InChI

InChIKey=FWKQNCXZGNBPFD-UHFFFAOYSA-N
InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including: https://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=73.2180 https://www.ncbi.nlm.nih.gov/pubmed/26401381

Guaiazulene is a blue compound. It is a derivative of azulene, guaiazulene is a bicyclic sesquiterpene that is a constituent of some essential oils, mainly oil of guaiac and chamomile oil. Guaiazulene is an U.S. FDA-approved cosmetic color additive. Guaiazulene is used in the formulation of bath products, cleansing products, depilatories, hair bleaches, hair conditioners, hair dyes and colors, hair straighteners, permanent waves, skin care products and skin fresheners. Guaiazulene has antioxidant, antifungal, antimicrobial, anti-inflammatory, anti-spasmodic, anti-ulcer, antitumoral activities and relaxant properties. Common side effects are: iarrhea, constipation, etc.

Originator

Šorm, F.|Zaoral, M.|Herout, V.
1
Curator's Comment: Isolation from chamomile oil.

Approval Year

2018
436
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
Inhibitor
8297
 9.8 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
ANZUWEI

Approved Use

It is usually used in the treatment of gastric ulcer.

Launch Date

1976
Primary
Approved
8429
ANZUWEI

Approved Use

It is usually used in the treatment of gastritis.

Launch Date

1976
Primary
Approved
8429
Ophthalmo-Azulen

Approved Use

It has been used for ocular burns and corneal burns.
Primary
Approved
8429
Ophthalmo-Azulen

Approved Use

Ophthalmo-Azulen is used in adults and children for eyelids, conjunctiva and cornea injure treatment, to accelerate the healing process after removing foreign bodies from the cornea.
PubMed

PubMed

TitleDatePubMed
[Use of garmastan in the prophylaxis and therapy of sore nipples of the breast].
2001
Synthesis of new azulene derivatives and study of their effect on lipid peroxidation and lipoxygenase activity.
2002 Jul
Intraindividual comparison of two different skin care conceptions in patients undergoing radiotherapy of the head-and-neck region. Creme or powder?
2002 Jun
Synthesis and antioxidant activity of 3-substituted guaiazulene derivatives.
2002 Jun
Solvatochromism, halochromism, and preferential solvation of new dipolar guaiazulenyl 1,4-benzoquinone methides.
2003 Apr 21
Calenzanane sesquiterpenes from the red seaweed Laurencia microcladia from the Bay of Calenzana, Elba Island: acid-catalyzed stereospecific conversion of calenzanol into indene- and guaiazulene-type sesquiterpenes.
2003 Dec 5
Torilin from Torilis japonica, as a new inhibitor of testosterone 5 alpha-reductase.
2003 May
Moist skin care can diminish acute radiation-induced skin toxicity.
2003 Oct
Temperature dependence of the infinite dilution activity coefficient and Henry's law constant of polycyclic aromatic hydrocarbons in water.
2004 Aug
A convenient synthetic route to benz[cd]azulenes: versatile ligands with the potential to bind metals in an eta5, eta6, or eta7 fashion.
2004 Oct 25
Comparative analysis of the oil and supercritical CO(2) extract of Artemisia arborescens L. and Helichrysum splendidum (Thunb.) Less.
2006 May 10
Optimisation of stir bar sorptive extraction and liquid desorption combined with large volume injection-gas chromatography-quadrupole mass spectrometry for the determination of volatile compounds in wines.
2008 Aug 22
Enhancement of Escherichia coli and Staphylococcus aureus antibiotic susceptibility using sesquiterpenoids.
2008 Nov
Benzo[cd]azulene skeleton: azulene, heptafulvene, and tropone derivatives.
2009 Dec 3
Quantification approach for assessment of sparkling wine volatiles from different soils, ripening stages, and varieties by stir bar sorptive extraction with liquid desorption.
2009 Mar 9
Effect of Matricaria chamomilla L. flower essential oil on the growth and ultrastructure of Aspergillus niger van Tieghem.
2010 May 15
Cytotoxic activity of guaiazulene on gingival fibroblasts and the influence of light exposure on guaiazulene-induced cell death.
2011 Feb
Patents

Patents

US2734931 A
1
US4755529 A
1

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Ophthalmic ointment in adults and children apply into the conjunctival sac or applied to the skin of the eyelids and around the eye 3 - 5 times per day until complete healing. Without consulting a doctor, do not use the medicine for longer than 10 days. https://pribalovy-letak.info/ophthalmo-azulen
Take 1 tablet (2 mg of the active ingredient) at a time, three times daily, before meals.
Route of Administration: Other
In Vitro Use Guide
Guaiazulene caused statistically important increases in total oxidative stress levels at concentrations higher than 100 µg/mL in rat neuron cell line.
Name Type Language
GUAIAZULENE
INCI   MART.   MI   WHO-DD  
INCI  
Official Name English
7-ISOPROPYL-1,4-DIMETHYLAZULENE
Systematic Name English
1,4-DIMETHYL-7-ISOPROPYLAZULENE
JAN  
Systematic Name English
KESSAZULEN
Common Name English
GUAIAZULENE (CONSTITUENT OF CHAMOMILE) [DSC]
Common Name English
GUAIAZULENE [MART.]
Common Name English
UROAZULEN
Common Name English
S-GUAIAZULENE
Common Name English
NSC-4714
Code English
VAUMIGAN
Common Name English
Guaiazulene [WHO-DD]
Common Name English
GUAIAZULENE [MI]
Common Name English
VETIVAZULEN
Common Name English
GUAIAZULEN
Common Name English
PURAZULEN
Common Name English
SILAZULON
Common Name English
1,4-DIMETHYL-7-ISOPROPYL-AZULENE
Systematic Name English
GUAIAZULENE [INCI]
Common Name English
AZULENE, 1,4-DIMETHYL-7-(1-METHYLETHYL)-
Systematic Name English
1,4-DIMETHYL-7-ISOPROPYLAZULENE [JAN]
Common Name English
Classification Tree Code System Code
WHO-ATC S01XA01
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
WHO-VATC QS01XA01
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
Code System Code Type Description
EVMPD
SUB14032MIG
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
ChEMBL
CHEMBL1408759
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
SMS_ID
100000092369
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
PUBCHEM
3515
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
DRUG BANK
DB13329
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
NSC
4714
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
DAILYMED
2OZ1K9JKQC
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
CAS
489-84-9
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
MESH
C004451
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
MERCK INDEX
m5860
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID7045996
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
WIKIPEDIA
GUAIAZULENE
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
FDA UNII
2OZ1K9JKQC
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
RXCUI
26290
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY RxNorm
DRUG CENTRAL
3272
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-701-2
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
CHEBI
5550
Created by admin on Fri Dec 15 16:19:29 GMT 2023 , Edited by admin on Fri Dec 15 16:19:29 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of GUAIAZULENE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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